Annrai O'Toole, CEO and Co-Founder

Annrai has a strong history founding and leading successful companies. His role as CEO is rooted in deep industry knowledge, backed by years of leadership, technical innovations, and successfully aligned teams. Prior to co-founding Utmost, Annrai served as European CTO at Workday, where he held several positions in both Product and Sales since becoming part of the team in 2008.

Stories by Annrai


Transforming The VMS Starts With Invoicing

In previous discussions, I’ve talked about why only 6% of spend is currently being captured in a traditional VMS. Most sourcing and hiring decisions...


Getting work done with Utmost Front Door

At Utmost, we are transforming how work gets done. This means finding a more strategic approach to sourcing and engaging talent. This requires less...


Utmost 2021 In Review - And A Look Ahead To 2022

2021 has been a big year for Utmost - in more ways than one. For us, 2021 has been a significant turning point: We’ve tripled our customers in...


Why Front Door?

As we launch our Q2 2021 release of Utmost, we are focusing on one of the coolest and most innovative features: Utmost Front Door.


Announcing Our Series B

We’re delighted to announce that we’ve successfully concluded our Series B, added Mosaic Ventures as a new investor, and raised $21M to help fund our...


The Extended Workforce

Utmost was established to change the conversation about this critical part of the workforce. We believe that the extended workforce is vital and...

Get notified of the latest insights on extended workforce management

Subscribe to get invitations to exclusive events, interviews with contingent workforce program leads, and the latest research on best practices for extended workforce programs for Workday customers.